Would this be a cool outfit for me to wear on the first day of high school?

Loving the jeans and the shoes! Not to sure about the top, for a first day at high school, I think your reveling a little too much about your personality. Just wear something casual to start with then gradually start wearing clothes that suit to your personality more. But from what I have said, don't feel like you should wear something your not comfortable in, just wear something loose, casual and something comfortable! Hope this helped!:')